Lithium borohydride → HCID 58012359, compound

Participants

Reaction Steps

To a solution of isopropyl [4-chloro-2-[(4-chloro-2-methoxy-6-methylphenyl)amino]-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]acetate (453 mg, 0.920 mmol) in tetrahydrofuran (5 mL) was added lithium tetrahydroborate (60 mg, 2.76 mmol), and the mixture was refluxed for 2 hr. After cooling, the reaction mixture was quenched with water and extracted with ethyl acetate (×2). The combined organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residual solid was recrystallized from ethyl acetate-n-hexane to give the title compound (250 mg, 0.573 mmol, 62.3%) as a colorless crystal. The filtrate was concentrated in vacuo, and the residual solid was recrystallized from ethyl acetate-n-hexane to give the title compound (91 mg, 0.209 mmol, 22.7%) as a colorless crystal. Total amount: 341 mg, 0.781 mmol, 85%.

Provenance & Evidence